Chris Webby wants detractors to listen to “Fragile Lives.” Released last December, the Norwalk, Connecticut-native salutes fallen homies, while simultaneously imploring presumably anyone listening to strive for their dreams before it’s too late. It’s the type of commentary rarely associated with Webby, unfortunately. His largely be young, have fun, get drunk reputation supersedes the contextual range and lyrics-first emphasis cemented firmly at the foundation of everything the freestyling free-spirit works tirelessly to embody. But this ironic contradiction isn’t lost on him. Make no mistake about it, Chris Webby is aware and in control of every minutia of his burgeoning career.

Fresh off the release of his first commercial EP, There Goes The Neighborhood, and currently in the midst of a self-funded 40-plus city tour, Chris Webby reveals an impressive amount of insight in this interview with HipHopDX. The 23-year old discusses the roots of his crew, Homegrown Entertainment, details his intricate writing process, shares the nervousness felt when he had to kick raps for Dame Dash, and how he’s on “the best streak of his life.”

HipHopDX: How’s the tour going so far?

Chris Webby: Man, it’s been a great fucking ride. This is my first time on a tour bus and we’re just having a good fucking time, basically.

DX: You’re in North Hampton, New Hampshire tonight, right?

Chris Webby: Yeah. So far this is the fourth of many [shows]. We’re doing like 40-something shows total.

DX: It’s pretty impressive what you’ve been able to do branding wise and marketing wise. You guys seem like a one-stop-shop.

Chris Webby: Yeah. No label, none of that. It’s difficult to try to balance it all and pay for everything. I’m paying for my own tour bus, for example. Everybody is getting their per diem. It’s tough at times but now we’ve finally reached enough success to where the machine is running smoothly. But so much of the money is put right back into the project. It is what it is. I love this lifestyle.

DX: Who’s on your team? Do you consider yourselves an independent label?

Chris Webby: We’re working on starting our own LLC, which is Homegrown Entertainment. The name alone speaks to exactly what this whole thing has been about. It’s just been me and my manager, Dana [Biondi]. Obviously we’ve added a lot to the team but me and him really kind of run the show and keep everything moving the way it needs to be.

DX: He’s in the background of a lot of video interviews you’ve done. You guys seem like good friends. He’s talking junk about your kicks on camera and stuff like that. Does that make it easier or more challenging to have close friends around while building your career? Have you stumbled into any “yes men” situations yet?

Chris Webby: I definitely keep people around who are going to be straight up with me. I keep my friends from [when I was] growing up close because I know a lot of people you meet in this industry are full of bullshit. It’s lot of bullshit. There’s a lot of fake people. I keep a lot of friends around me who I know will always tell me the truth; tell me what’s best for me. That’s really important, too. I’m just a humble person to begin with, so there’s no crazy shit. I’ve met some rappers who were pretty cocky and that can cloud your decision making skills. But when it comes to being in the studio, that’s my favorite part. That, and performing. The creative sides to everything are my favorites. I’ve never been great at business, I’m not going to lie to you. That’s why I have people to help me with all that. They keep everything running on that end, and I keep all the creative shit running. It works somehow.

DX: It’s absolutely working. Just watching your progress and your team’s efficiency over the past three or four years, it’s absolutely working.

Chris Webby: Thank you, man. Thank you. I think a lot of people are still getting to see that. But I also feel like a lot of people don’t know what’s going on in the camp over here – how much hard work we put in. People don’t know more than my name, and maybe a track or two, and a judgement off of that. I really want to get that out to people. People should just look into what we’ve done and don’t judge me off of one or two tracks. There’s all kinds of tracks that I’ve put out there. I’ve put out six mixtapes and an EP at this point.

DX: How have you been able to galvanize your fan base nationally? How have you been able to spread from Connecticut to having kids in Ohio know all the words to your joints?

Chris Webby: It’s been really gradual, for sure. It’s just been a lot of word of mouth. The internet plays a huge role. It definitely started in Connecticut and New York. Then Massachusetts it spread to. Then it kind of got up to Vermont, then down as far as [New] Jersey, then out to Pennsylvania. It just kept spreading. But you’ve got to think that all those kids in high school from New York and Connecticut, a lot of them go to college and they’ll take that music with them and show kids from other states. Then those kids will go back home and show it to their friends. It’s been a crazy year. I always see a burst in the fan base every time a new group of kids go to college because that’s a new group of kids that are being exposed to it for the first time.

DX: That’s a great point. You told a story one time about going to DD172, Dame Dash’s studio in Manhattan. You said that he asked you to spit for him before you went into the studio with Ski Beatz. What was going through your mind the moment Dame Dash asked you to spit for him? Were you nervous?

Chris Webby: I mean, yeah. At that point especially because that’s when I was first getting taken around the industry. Between then and now, I know how to carry myself so much better in those situations. I was just kind of like, “Holy shit.” This was one of the first important Hip Hop figure heads that I’ve met, if not the first, really. To have Ski Beatz there at the computer [who’s] obviously a production legend. I just knew I had to come with some fire. I didn’t freestyle. It was a written, no doubt. But it impressed him.

DX: I think moments like those really define being an emcee. You talk a lot about appreciating the competitive aspect of Hip Hop; wanting to improve lyrically first before worrying about making a hot song.

Chris Webby: Yeah. You have to be ready to answer the call if it comes. There are some situations you get put in and it’s either do or die. I could’ve just not spit for Dame Dash that night. I could’ve choked. Hip Hop is so spontaneous. Freestyling is so spontaneous. I’ve been freestyling every night on tour. We’ve just been getting hammered in the back of the bus [and freestyling]. Some of my boys freestyle a little bit. They’re not great, but then I come in and do what I do. There’s definitely a spontaneous aspect. Growing up battling, that shit was so spontaneous. You just meet a kid at a party and he starts talking a little shit, you know. It’s like, “Back up your shit then. Let’s go.” A lot of time kids would just back right down because they weren’t ready. Now, unfortunately for me battling can never really be spontaneous for me again now that people know who I am. That’s why I don’t really battle anymore because there’s really no point. If someone steps to me at a party, he could know everything about me and I know nothing about him. He could have a pre-written because he knew I was gonna be there. I do miss that aspect.

DX: Does Hip Hop still look competitive to you now that you’re touring and just about part of the machine? Has that perspective changed?

Chris Webby: It definitely is. Unfortunately, I get put into the category with all the white rappers. We all have this competitiveness with each other. I think that’s ridiculous, to be honest with you. Me, Mac Miller, Machine Gun Kelly, Yelawolf – my style is nothing like any of them. The only thing we have in common is our skin color. I get it. We are White rappers. There are far less of us. I get it. I’m the White guy. I get it. But our styles are so different. People just got to listen a little bit more when it comes to that shit. But there’s still definitely a competitiveness in Hip Hop. I think a lot of people get comfortable once they start buzzing. They lose their hunger. You have to stay hungry. You have to keep trying to outdo the last thing you did. Everything has to be better than the last one. I think the fact that it’s been a gradual ride for me – it wasn’t just some overnight fucking smash single – has kept me hungry. It’s kept me really perfecting my craft more so than it would have if I had had that over night smash. I’m still hungry. There’s a lot more out there I want to get. Obviously, I’m a lot happier now that I can pay for my own fucking meals and I have some money in my pocket because I really didn’t back in the day. Other people had to pay for my studio time. I had to borrow money from my mom to put fucking gas in my car. Now, shit’s a lot better than that. I’m not ready to quit now, I’ll tell you that much.

DX: Was there a difference putting together There Goes The Neighborhood knowing that this was going to be your first commercial release? Did you approach it differently than your previous mixtapes?

Chris Webby: Yeah, we did approach it differently it terms of beat selection. Obviously we tried to go as sample free as possible. We just really wanted every track to have a reason to be on there. Some people could argue that every track didn’t have a reason of being on there. But for the most part, I think the reviews have collectively been that this is very solid first project to put on iTunes. The material’s been great to perform, too. A lot of those songs go really hard on stage. That’s a good thing, too.

DX: It seems like you have to think about something like that ahead of time as an artist.

Chris Webby: Definitely, because after the last tour, I was like, “Alright, after this next album I release, we’re going to have a tour after it for the project. Obviously I’m going to do all my old shit, too, but I definitely want to have some bangers on here that will make the crowd go nuts.” It’s definitely in the back of your mind. And on certain songs that you know are going to go crazy on stage, you worry less about filling up all those syllables. You’re picturing yourself rapping it on stage, and you’re like, “Alright, I’m going to be out of breath if I try to put all these syllables in here. So I can say the same thing but cut out a couple words right here that I don’t really need.” You just got to think ahead. I have ADD like a motherfucker. I really do. I think that’s part of the reason why I can freestyle so well, because my mind just goes all over the fucking place. It’ll just tap into weird metaphors and shit I haven’t thought about in six or seven years and it’ll just come out when I’m freestyling somehow. There’s just so many things I think about creative process wise, but that’s the shit rappers have to think about. People think it’s so fucking easy. It’s not, really, if you take it seriously.

DX: That’s some real depth. Sometimes I question how many artists think about the minutia.

Chris Webby: I don’t think a lot of them do, really. It’s cool. There’s different kinds of Hip Hop and some of them don’t require that complex of a thinking process. But this is my job and I do take it very fucking seriously. I’m not the kind of dude that’s gonna get fucking black-out drunk before he goes on stage; or smoke a fat blunt and be too high to really put in a good performance. This is my fucking job and I do take it very seriously. I have a great time. I get fucking hammered every night, no doubt. But after the show.

DX: You know, you mentioned briefly once that you took an E pill once before a show.

Chris Webby: Yeah! That was way back when and that was not a good fucking idea.

DX: Describe that show. What’s it like rolling on E on stage?

Chris Webby: That was at Hofstra [University] when I was still there. It was pretty much like one of my first shows. And I can’t remember that much about it other than it was just an absolute cluster-fuck. I had like three or four friends on stage with microphones for absolutely no reason. I don’t even use a hype-man anymore. I just do it myself because I think it’s a more tactful approach to the way my songs are, at least. That show, I was just up there fucking rolling face like, “What the fuck?!” Like 25 of my friends showed up. I was like, “What’s up guys! I see you everyday but I’m on stage now and I’m gonna fucking rap!” It was really weird. [Laughs] Dude, I’ve had some experiences, I’ll tell you that. I’ve definitely, definitely paid my dues. I can say that without second guessing myself whatsoever.

I remember one time back in the day, somebody got me to open for Wu-Tang [Clan]. It was when Raekwon, [Ghostface Killah], and [Method Man] released Wu-Massacre. It was at Nokia Theatre. This was when I was maybe two mixtapes in, so nobody really knew who the fuck I was. And they put me on before Wu-Tang, which in itself is a fucking horrible idea. Wu-Tang fans are not trying to have some fucking little Connecticut kid run out there and do anything, let alone run out and my fucking CD doesn’t work. I turn around and my fucking deejay’s looking at me like, “Uh, dude, I don’t know.” I’m just sitting there looking at a fucking sold out Wu-Tang crowd like “Uhhhhh…” [Peter] Rosenberg from HOT97 was on the other deejay table. I turned to him and was like, “Yo, dude, just drop a beat. I’m gonna freestyle real quick, then I’m gonna get the fuck out of here.” Thank God I know how to freestyle because it at least salvaged [the show] a little bit. I’ve had better experiences in Hip Hop, but it’s definitely something to remember.

DX: How did the crowd respond to the freestyle?

Chris Webby: I think a good portion of them definitely hated me. I think the ones who realized the technical difficulties were like, “Oh shit, his shit got fucked up and he freestyled. I can respect that.” That was really all there was to it at that point.

Chris Webby: Yeah, man. I was walking out and people gave me daps like, “That was dope. You handled your shit up there. A lot of people would’ve cracked.” And a lot of people would’ve cracked. People would’ve started crying. That was some very intimidating shit. When I say I’ve been through some shit, [that’s what I mean]. There have been plenty of shows with ten people there back in the day. I’ve done sweet 16 [birthdays], bar mitzvahs, graduation parties. I did a fucking middle school graduation party. Imagine the fucking looks on the parents faces when they heard what the fuck I was talking about. And I did it for like 50 bucks and a pizza or something like that. I used to perform for fucking food if that was part of the bargain. Food and 50 bucks was a good check back in the day.

DX: I agree with you, man. I love [Dr. Dre’s] 2001, too. Everyone was hitting on all cylinders on that project. The beats, the rhymes, it was great.

Chris Webby: That was my favorite era of rap. Back when it was Eminem, Dr. Dre, Nate Dogg was doing the hooks. Xzibit was fucking with all of them. Snoop [Dogg and] Busta [Rhymes] was killing shit back then. And they all worked together. That was honestly, in my opinion, the golden era of what I saw in Hip Hop. Jay-Z and Eminem did “Renegade” together. There was a lot of dope shit happening. And that’s what actually got played on the radio. Like, “Break Ya Neck” by Busta Rhymes was actually on the radio. Now when I listen to the radio I want to fucking puke. They used to play like “Still D.R.E.” and “Forgot About Dre” on the radio. I’m not trying to fucking take shots, but I’m not a fan of the normal radio these days.

DX: The “What I Do” video is cool. It looks like you guys are having fun and that’s what I think about when I think about Chris Webby. Earlier in the interview you mentioned that if people do the research, they’d understand the range that you really have. But songs like “What I Do” end up being the joints that people associate with you…

Chris Webby: Exactly. And that’s partially our fault because that’s the one we dropped for the video if you really think about it.

DX: What’s the logic behind releasing songs like that first? Is it the mass appeal type approach? Is it an attempt to get spins on major outlets?

Chris Webby: I think to a certain degree. That was the first one we leaked, so in theory that was gonna be the first one we did a video for. But I thought we were going to have a video for that right before the EP dropped or immediately after. That shit was late. The one thing I can say about our approach that is lacking is our video campaign. No doubt about it. We’re about to step that up. But you also have to factor in what we’ve been trying to do and the funds we’ve had to do it with. Shooting a video wasn’t really an option back in the day. So we kind of got used to not really worrying about videos because we just didn’t have the bread for it. Now that we do, it’s still kind of on the back burner. One hundred percent, we need to make that more of a priority. We just shot two videos before we left on tour so there’s gonna be one for “I’m Gone” and “Bounce,” also. I think a good artist needs to be able to critique themselves and critique their approach. In a lot of areas, I think I’m very strong. But our video campaign is definitely slacking in comparison to someone like Mac Miller who I can wholeheartedly say his video campaign is crazy. But that’s something with time, and now that we have more money coming in, will definitely be fixed. I’m not stressing it.

But yeah, people hear songs like “What I Do” [and think that’s all I’m about]. Yeah, that’s a cool song, but that’s basically a generic Chris Webby song. There’s so many more songs that talk about shit that I’ve been through in my life that people can relate to. Honestly, if I was gonna tell anyone who has a sour opinion about me, [I’d say] to look up the track that I dropped in December called “Fragile Lives.” It’s gonna be on the next mixtape, but it hasn’t been on anything yet.

Chris Webby: Thank you. It is, and it will give people a different opinion and show that I’m capable. A lot of artists aren’t capable of doing a song like that. They get stuck in their little lane and that’s all they’re comfortable with. I can do other shit other than rapping about weed and girls. I do that all the time it’s just that people don’t necessarily hear it. I love weed, and girls, and partying, and drugs to a certain degree, but I’m on probation so not so much. [Laughs] I love having fun. I’m a fucking wild motherfucker sometimes, I’m not going to lie to you.

DX: What are you on probation for?

Chris Webby: It’s a long story. My friends robbed a drug dealer back when I was at Hofstra. Somehow I ended up driving the car to do so. Long story short, a lot of trouble and the dudes ratted me out after giving me all the shit to bring back to my crib. I ended up with the short end of the stick and basically it sucked. What sucks even more is that I’ve heard people on Twitter be like, “Yo, Chris Webby’s a snitch,” and that couldn’t be any further from the fucking truth. It’s crazy. But that just shows you how rumors and shit spread in Hip Hop. It’s ridiculous. People were saying Asher Roth is gay. People were saying this and that. I guess you just have to fucking deal with it, I guess.

DX: The pains of celebrity.

Chris Webby: Yeah. But that’s a shitty rumor, especially when it’s literally the opposite. It’s just a shitty rumor. I’d rather people be saying that I was gay, you know.

DX: I don’t know if you’d want that.

Chris Webby: People could say I’m gay, bro, but I’m fucking banging really hot chicks. In fact, I’m on the best streak of my life so I really wouldn’t mind.

DX: That’s a good point.

Chris Webby: What it comes down to is rumors in Hip Hop. If it’s not true then it’s like, “Whatever, bro.” You see the tabloids and shit. These poor fucking celebrities, bro. They get ripped apart and it’s usually not even true. It’s crazy.

DX: With everything you’ve experienced and everything you’re currently accomplishing, after starting to rhyme in the fifth grade after once realized you didn’t want to study bugs when you grow up, what still surprises you about Hip Hop?

Chris Webby: I mean, I learn something new everyday. The thing about doing it independently is you have to just learn yourself and a lot of times that learning is through your own mistakes. We have made plenty of mistakes along the way, but you learn and you never do it again. That’s the only way when you don’t have someone literally guiding you along like a label would. Paying for this. Telling you what to do here and there. At the same time, I think it’s so much more raw to do it this way. You learn so much. You earn your stripes so much more than just having an overnight fucking ringtone smash. I wouldn’t trade those stripes for a fucking check any day.